Real Estate Investment Properties for Sale in Winnetka, IL
Looking for investment property in Winnetka, IL with high ROI ?
Explore a variety of short-term homes & houses in Winnetka, IL. Invest wisely with VRBO & Winnetka, IL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Winnetka, IL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
755 Lincoln AvenueWINNETKA, ILThe iconic front porch has you at hello...welcoming you to this exceptionally updated clas... |
5 beds | 5 baths | 5,904 sq.ft. |
$2,595,000 |
Airbnb cash on cash: N/A
|
471 Linden StreetWINNETKA, ILWonderful right-size home in the heart of Winnetka...just steps from town, train, library ... |
3 beds | 2 baths | 1,927 sq.ft. |
$575,000 |
Airbnb cash on cash: -0.19%
|
1161 Pine StreetWINNETKA, ILWelcome to your serene oasis nestled on a private .85-acre lot in the heart of Winnetka. T... |
4 beds | 3 baths | 3,667 sq.ft. |
$2,195,000 |
Airbnb cash on cash: N/A
|
342 Rosewood AvenueWINNETKA, ILSophisticated perfection on an extra wide lot in one of Winnetka's most picturesque neighb... |
4 beds | 5 baths | 4,585 sq.ft. |
$1,995,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winnetka, IL
There are 8 properties for sale in the city of Winnetka . The median list price in Winnetka is $1,549,000 and the average price per square foot is $450. In October 2025, the average monthly cash on cash return in Winnetka is N/A%. The average monthly rental income in Winnetka is $4,026.